8-methoxy-5H-pyrido[4,3-b]indole | 96473-59-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 8-methoxy-5H-pyrido[4,3-b]indole
• 英文别名: 8-Methoxy-5h-pyrido[4,3-b]indole
• CAS: 96473-59-5
• 化学式: C₁₂H₁₀N₂O
• mdl: MFCD18803721
• 分子量: 198.224
• InChiKey: JDDPTXUPKJEPTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-methoxy-5H-pyrido[4,3-b]indole 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 7,9-Dibromo-8-methoxy-5H-pyrido[4,3-b]indole
  参考文献：
  名称：

  Structure-activity relationship of bromoeudistomin D, a powerful Ca2+ releaser in skeletal muscle sarcoplasmic reticulum

  摘要：

  Bromoeudistomin D and 9-methyl-7-bromoeudistomin D which have a beta-carboline skeleton are powerful Ca2+ releasers from skeletal muscle sarcoplasmic reticulum exhibiting caffeine-like properties. We examined the effects of bromoeudistomin D analogues on Ca(2+)-induced Ca2+ release from skeletal muscle sarcoplasmic reticulum. Among bromoeudistomin D analogues, the Ca(2+)-releasing activities of carboline derivatives were higher than those of carbazole derivatives, suggesting that a carboline skeleton is significantly important for the manifestation of Ca(2+)-releasing activity and Ca2+ sensitivity of Ca(2+)-induced Ca2+ release. On the contrary, the analogues which have a carbazole skeleton and bromine at C-6 inhibit both Ca(2+)- and caffeine-induced Ca2+ release. 9-Methyl-substitution of the analogue elevated its Ca(2+)-releasing activity. Moreover, there is a close correlation between the enhancement of [3H]ryanodine binding to sarcoplasmic reticulum by the analogues and the activation of Ca2+ release by them. Bromoudistomin D analogues may provide valuable information about the structure-function relationship of the ryanodine receptor/Ca2+ release channels in skeletal muscle sarcoplasmic reticulum.

  DOI：

  10.1016/0922-4106(95)90040-3
• 作为产物：
  描述：

  (4-甲氧基苯基)肼 在 硫酸 、 palladium 10% on activated carbon 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 生成 8-methoxy-5H-pyrido[4,3-b]indole
  参考文献：
  名称：

  γ-咔啉-吩噻嗪偶联物同时作为 NMDA 受体阻滞剂和胆碱酯酶抑制剂的评价

  摘要：

  阿尔茨海默病 (AD) 是最常见的痴呆症。它与主要由中枢神经系统中胆碱能和谷氨酸能信号传导的进行性缺陷引起的记忆和其他认知功能障碍有关。乙酰胆碱酯酶和的离子型谷氨酸受体的抑制剂Ñ甲基d天冬氨酸（NMDA）受体家族目前批准作为AD的治疗剂。我们之前使用基于细胞的 NMDA 受体介导的谷氨酸盐诱导的兴奋性毒性试验表明，双-γ-咔啉结合物是有用的 NMDA 受体阻滞剂。然而，这些化合物也可作为亚纳摩尔 AChE 抑制剂，在体内应用时可能会导致严重的抗胆碱能副作用. 在这里，我们评估了包含通过丙酰基间隔基连接到吩噻嗪的 γ-咔啉的新结构。这些化合物优于之前表征的双-γ-咔啉结合物，因为它们无需季吡啶N原子即可阻断 NMDA 受体，并以 0.54–5.3 µM 的中等 IC 50值抑制 AChE 。此外，这些新化合物对丁酰胆碱酯酶 (BChE；IC 50  = 0.008–0.041 µM)的抑制显示出相当大的选择性，这可能有利于

  DOI：

  10.1016/j.bmc.2021.116355

文献信息

• 一种8-甲氧基-5H-吡啶并[4,3-b]吲哚及其合 成方法
  申请人：南通大学

  公开号：CN111892593B

  公开（公告）日：2021-11-16

  本发明属于有机合成技术领域，涉及一种8‑甲氧基‑5H‑吡啶并[4,3‑b]吲哚及其合成方法。本发明提供的合成方法为：以1‑(4‑甲氧基苯基)肼为原料，经酮胺缩合、磺酰化、活泼氢保护、消去及水解反应五步反应制备了8‑甲氧基‑5H‑吡啶并[4,3‑b]吲哚，合成路径简单，成本低，效率高。
• Microwave-Enhanced Fischer Reaction: An Efficient One-Pot Synthesis of γ-Carbolines
  作者：Yongzhou Hu、Jing Chen、Weiliang Chen

  DOI：10.1055/s-2007-992411

  日期：2008.1

  γ-Carbolines were obtained in a simple one-pot Fischer arting from N-acetyl-3-bromo-4-piperidone hydrobro-reaction starting from N-acetyl-3-bromo-4-piperidone hydrobromide and substituted arylhydrazine hydrochlorides in acidic media under microwave irradiation or by a thermal process. The optimization procedures are reported in detail, and the results from micro-wave processes are compared with conventional

  γ-咔啉是在简单的一锅 Fischer arting 中从 N-乙酰基-3-溴-4-哌啶酮氢溴酸盐反应中获得的，反应起始于 N-乙酰基-3-溴-4-哌啶酮氢溴酸盐和取代的芳基肼盐酸盐在酸性介质中微波辐射或通过热处理。详细报告了优化程序，并将微波工艺的结果与传统工艺进行了比较。
• Evaluation of Homobivalent Carbolines as Designed Multiple Ligands for the Treatment of Neurodegenerative Disorders
  作者：Robert Otto、Robert Penzis、Friedemann Gaube、Oliver Adolph、Karl J. Föhr、Paul Warncke、Dina Robaa、Dorothea Appenroth、Christian Fleck、Christoph Enzensperger、Jochen Lehmann、Thomas Winckler

  DOI：10.1021/acs.jmedchem.5b00958

  日期：2015.8.27

  Neurodegenerative diseases represent a challenge for biomedical research due to their high prevalence and lack of mechanism-based treatments. Because of the complex pathology of neurodegenerative disorders, multifunctional drugs have been increasingly recognized as potential treatments. We identified homobivalent gamma-carbolinium salts as potent inihitors of both cholinesterases, N-methyl-D-aspartate receptors, and monoamine oxidases. Homobivalent gamma-carbolines displayed similar structure activity relationships on all tested targets and may present promising designed multiple ligands for the treatment of neurodegenerative disorders.
• Discovery of an ellipticine derivative as TLR3 inhibitor against influenza A virus and SARS-CoV-2
  作者：Yue Pan、Qiuyue Fu、Yinyan Li、Jie Yang、Kui Cheng

  DOI：10.1016/j.bmcl.2024.129672

  日期：2024.3
• ECTONUCLEOTIDE PYROPHOSPHATASE-PHOSPHODIESTERASE-1 INHIBITORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  申请人：[en]LEGOCHEM BIOSCIENCES, INC.

  公开号：WO2023242631A1

  公开（公告）日：2023-12-21

  The present disclosure relates compounds for inhibiting ectonucleotide pyrophosphatase/phosphodiesterase-1 (ENPP-1), or a pharmaceutically acceptable salts thereof.